


Dean's Favorite Holiday

by braezenkitty



Category: Supernatural
Genre: Castiel/Dean Winchester First Kiss, First Kiss, Fluff, M/M, Valentine's Day, Valentine's Day Fluff
Language: English
Status: Completed
Published: 2019-02-15
Updated: 2019-02-15
Packaged: 2019-10-29 04:06:23
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,080
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17800754
Author URL: https://archiveofourown.org/users/braezenkitty/pseuds/braezenkitty
Summary: A bit of self-indulgent fluff written for Valentine's day. Dean and Cas finally get their shit together.





	Dean's Favorite Holiday

**Author's Note:**

> Yeah, I know it's late. But today's my birthday so I do what I want.

This was supposed to be Dean’s favorite day of the year. Unattached Drifter Christmas. The day when lonely girls in search of romance would let a guy like him into their bed for one night, and he could disappear in the morning and pick himself up some discounted chocolate.

Only this year was different. Maybe this day had been different for a while, if Dean was being honest with himself.

He didn’t want some random girl, or some random guy, for that matter. He wanted a very specific Valentine, and he had no idea how to go about getting said Valentine to be his.

Well, desperate times called for desperate measures.

“Hey, Sam. I need your advice.”

Sam looked up from his book, lifting an eyebrow. “You need… my advice. About what?”

Dean cleared his throat, looked around the library to make sure they were alone. “About like, Valentine stuff.”

“Valentine stuff.”

Dean gave Sam an annoyed look.

“Okay, Mr. Unattached Drifter Christmas… lemme get this straight—” Sam said, putting down his book.

“Well, not exactly straight,” Dean mumbled, shoving his hands in his pockets and staring at his feet.

Sam’s mouth dropped open. “Did—did you just come out to me?”

Dean cleared his throat again, glanced at Sam, then back at his feet. “Maybe.”

“Okay,” Sam said, leaning forward in his seat. “Okay, well, I can’t say I’m all that surprised. But what exactly do you need advice about?”

“Well, there’s this certain someone,” Dean said, pulling out a chair and sitting. “And I want to do something special for them, show them how I feel. But they’re not into normal stuff, I don’t think. Actually I don’t really know. But I guess I don’t want to do the normal, boring stuff. I want to do something special.”

“Okay,” Sam said slowly. “Is this person someone I might know?”

Dean rubbed the back of his neck. “Maybe.”

“Alright, well, what kind of things do they like?”

“Um, you know, I don’t really know. When we hang out we tend to do what I want to do.”

“Well, maybe you should find out what they like to do and do that with them.”

Dean frowned. “I don’t even know if _they_ know what they like to do.”

Sam raised his eyebrows, then sat back in his chair with a sigh. “Look, Dean, just ask him— _them_ , if they want to hang out and let them choose the activity.”

“I want it to be special though.”

“It’ll be special. Even if he— _they_ ,” Sam said, clearing his throat, “even if they decide all they want to do is get burgers and hang out in the Dean cave drinking beer and watching your favorite movies. Spending quality time together is what’s important.”

Dean thought for a moment. He smiled. “Thanks, Sammy,” he said, pushing his chair back and standing. He walked to the library entrance, then stopped and turned around, clearing his throat. “Um, would you mind taking Jack and staying out somewhere tonight?”

Sam made the sturgeon face and nodded. “Must be someone pretty special if you’re bringing ‘em back here.”

“Yeah,” Dean said, ducking into the hallway to hide his dopey grin.

* * *

This was Castiel’s least favorite day of the year. He didn’t usually pay much attention to human holidays, but this one was the worst. All it did was remind him of his failures in romance. Every time he’d tried being romantic, he’d gotten it wrong. Or he’d gotten killed.

Only maybe this year would be different. Maybe this year he’d have the courage to say something, do something.

He didn’t want to let another year go by without trying. He wanted a Valentine, a very specific Valentine, though he had no idea how to go about getting said Valentine to be his.

He knew just who to ask for advice.

“Hello, Sam. I wonder if you might help me with something.”

Sam looked up from his book, eyebrows raised. “Sure, Cas. What’s up?”

“It’s about Valentine’s day. I need to know how to make Dean my Valentine.”

Sam seemed to choke on air, setting his book down and sitting up straight. “Wow, um, okay. You sure don’t beat around the bush,” he said, then mumbled, “like some people.”

“Like what?”

“Um, nevermind. So you want Dean to be your Valentine, huh?”

“I do,” Cas said, pulling out a chair and sitting. “I want to do something special for him, to show him how I feel. But I have no idea how to do normal human courtship. In fact I’m really bad at it. But I don’t want to screw this up, not with him. I want to do something special.”

Sam huffed a laugh and smiled, sitting back in his chair with a sigh. “Look, Cas, just be honest. I’m pretty sure you’re both on the same page, so just spend some time together and tell him how you feel.”

“I want it to be special though.”

“Oh, I have a feeling it’ll be special.”

“You seem very confident,” Cas said, squinting at Sam.

“Cas,” Sam said with a sigh, “go hang out, relax and have fun. Be yourself. Make your move.”

Cas nodded. “Okay, Sam.” He stood and walked to the archway, then stopped and turned to look back at Sam. “Oh, Sam—”

“Yes, I’ll take Jack and leave you two the bunker tonight.”

“Um, okay,” Cas said, frowning. “I was just going to say thank you.”

“Oh, um, you’re welcome.”

* * *

 “These burgers are very delicious,” Cas said through a mouthful of meat and cheese.

“Yeah, they are,” Dean agreed through his own mouthful. He swallowed and washed it down with a sip of beer. “Hey, um, thanks for eating with me tonight.”

“Of course, Dean. You know I love having burgers with you.”

Dean huffed a laugh and picked up a fry, popping it into his mouth. “Sometimes I wonder though.”

“Wonder about what?”

“If you actually like doing the stuff I like to do.”

“Dean,” Cas said, setting his burger down and wiping his hands on a napkin, “I enjoy spending time with you, whatever we’re doing.”

Dean’s cheeks bloomed with heat and he smiled down into his plate before shoving another fry in his mouth. “Yeah, okay, but what kind of stuff do _you_ like to do?”

Cas frowned and tilted his head. “Well, like I said, I enjoy spending time with you, and with Sam and Jack, and Claire when she’s around. Watching Netflix. Spending time outside.”

“You’re not really giving me much to work with,” Dean mumbled, taking another sip of beer.

“Not much to work with for what?”

Dean cleared his throat. “Nothing, nevermind. I got an idea. Finish your burger.”

“You have an idea for what?” Cas asked, squinting as he popped the last bite of his burger into his mouth.

“Just finish eating, it’s a surprise,” Dean said around his own last bite. He took a sip of beer to wash it down, then flagged down the waitress for their check. After dropping a couple twenties on the table to cover it, he rose from the booth and gestured for Cas to follow him.

They made their way out to the Impala and hopped in. Dean started her up and pulled out of the driveway, turning right instead of left to go back to the bunker.

“Where are we going?” Cas asked with an adorable look of confusion on his face.

“Told you, it’s a surprise,” Dean said, throwing a grin at Cas before focusing on the road.

They drove past the town limits, out where there were no more buildings or lights. Nothing but open fields surrounded them, and Dean drove another ten miles or so until he came across a small, lonely looking farm road and turned onto it. He drove a ways off the main road, then pulled over and shut off the car.

“Come on,” he said, patting Cas’s shoulder before getting out of the car and walking around to the trunk. He pulled out a blanket and walked back around to the front of the car. Cas stood by the open passenger side door, watching Dean.

“What are we doing out here?” Cas asked, finally shutting the door.

Dean spread the blanket over Baby’s hood then hopped up, scooting up until his back rested against the windshield. “Get up here and you’ll find out.”

Cas raised an eyebrow but did as Dean had, settling next to Dean on the hood. Their thighs brushed and a thrill ran through Dean.

“Now what?” Cas asked, his voice soft as if he didn’t want to disturb the quiet that had settled around them.

“Now we watch the stars,” Dean said, laying his head back against the windshield. He tried looking up at the sky, but Cas stayed sitting upright.  Being in Dean’s line of sight, Dean found he couldn’t look away from him. “You ever gone stargazing before?” Dean asked, keeping his voice low.

Cas shook his head as he gazed up into the night sky. “Not from this vantage point.”

Dean’s stomach sank. Of course, Cas was an Angel. He’d probably gone stargazing from space or some shit. Sitting on top of a car on Earth and looking up at the stars was probably nothing to him. He started to sit up, lifting up on his elbows, when Cas turned to look down at him.

“It’s beautiful, Dean,” he said with a soft smile. “Thank you.”

Dean cleared his throat. Cas’s face was only inches away. He glanced down at Cas’ lips, then back up to Cas’s eyes. “Um, you’re welcome,” he said softly. They watched each other in silence for a moment before Dean felt a blush creeping over his cheeks. “Aren’t you gonna, you know, watch the stars?”

“I find I like watching their reflections in your eyes better.”

Dean’s blush deepened and he huffed a self-conscious laugh as he looked away. He was glad it was dark.

“Does that make you uncomfortable?” Cas asked, a worried frown creasing his forehead.

“A little, honestly,” Dean said, instantly hating himself when Cas’s face fell and he looked away. “But not in a bad way,” he hurried to say, placing a hand on Cas’s shoulder.

Cas turned back to look at him. “I don’t want to make you uncomfortable, Dean,” Cas said, looking serious. “And I know I’m horrible at romance and courtship. But I’d really like to kiss you.”

Dean choked on air, sitting up straighter.

“I’m sorry,” Cas said dejectedly, looking away and moving to slide off the hood.

“Cas, wait,” Dean managed, grabbing a handful of his trenchcoat. “You just caught me off guard. Which is ridiculous, seeing as I brought you out here to be romantic and all. I’m not so great at the whole romance and courtship thing either.”

Cas turned slightly, not yet meeting Dean’s eyes.

“Come back here,” Dean said softly, tugging at Cas’s coat.

Cas scooted back onto the hood, angling his body towards Dean and looking at him curiously.

“I’d really like to kiss you too,” Dean said, reaching a hand up to angle Cas’s face towards him. He inhaled deeply, trying to calm the butterflies in his stomach as he slowly leaned forward.

Cas’s eyes widened and he licked his lips, and Dean kissed him, slowly, tentatively.

Cas made a soft sound and pressed forward, a hand coming to rest on Dean’s waist. Dean’s mouth fell open on a sigh and his tongue darted out, tasting Cas’s lips. Cas opened to him and the kiss deepened, their tongues sliding against each other.

Dean nipped at Cas’s bottom lip and with a growl, Cas was suddenly pressing him against the windshield, his torso covering Dean’s. Dean wrapped his arms around Cas’s neck and gave as good as he got, kissing Cas like he’d been dreaming about for years.

Cas pulled back suddenly and Dean’s stomach dropped. Had they moved too fast? Was Cas overwhelmed? But Cas didn’t move far, so maybe things were okay.

“Dean,” Cas said, voice sounding absolutely wrecked, “I have something very important to ask you.”

Dean frowned in confusion. “Okay, shoot.”

“Does this mean you’re my Valentine?”

Dean laughed, tightening his arms around Cas’s neck to draw him closer. “Hell yes this means I’m your Valentine. And you’re mine.” He pulled Cas down for another kiss.

“I think this just became my favorite holiday,” Cas mumbled between kisses.

Dean couldn’t agree more.

**Author's Note:**

> Bonus:
> 
> "Come on, Jack, grab your bag and let's get out of here," Sam said, slinging his duffel bag over his shoulder and starting up the bunker stairs.
> 
> "I still don't understand why we have to leave," Jack said, though he followed.
> 
> Sam sighed heavily. "Well, I guess you were gonna need 'the talk' soon anyway. Dean and Cas owe me big time."


End file.
